Neopentyl glycol diglycidyl ether

Names
IUPAC name

2-[[2,2-dimethyl-3-(oxiran-2-ylmethoxy)propoxy]methyl]oxirane

Other names

Neopentyl glycol diglycidyl ether; 1,3-Bis(2,3-epoxypropoxy)-2,2-dimethylpropane; 2,2'-((2,2-Dimethyl-1,3-propanediyl)bis(oxymethylene))bis(oxirane); CCRIS 2640; Diglycidyl ether of neopentyl gylcol; EINECS 241-536-7; Heloxy WC68; UNII-9288EM7AOW; Oxirane, 2,2'-((2,2-dimethyl-1,3-propanediyl)bis(oxymethylene))bis-; Propane, 1,3-bis(2,3-epoxypropoxy)-2,2-dimethyl-

Identifiers

CAS Number

* 17557-23-2

3D model (JSmol)

* Interactive image

ChEMBL |

* ChEMBL1587512

ChemSpider |

* 26599

ECHA InfoCard | 100.037.745
EC Number |

* 241-536-7

PubChem CID

* 28594

CompTox Dashboard (EPA)

* DTXSID8025707

InChI

* InChI=1S/C11H20O4/c1-11(2,7-12-3-9-5-14-9)8-13-4-10-6-15-10/h9-10H,3-8H2,1-2H3

Key: KUAUJXBLDYVELT-UHFFFAOYSA-N

SMILES

* CC(C)(COCC1CO1)COCC2CO2

Properties

Chemical formula

| C11H20O4
Molar mass | 216.275 g/mol
Hazards
GHS labelling:[1]

Pictograms

Signal word

| Warning

Hazard statements

| H315, H317

Precautionary statements

| P261, P264, P272, P280, P302+P352, P321, P332+P313, P333+P313, P362, P363, P501

Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Infobox references

Chemical compound

Neopentyl glycol diglycidyl ether (NPGDGE) is an organic chemical in the glycidyl ether family. It is aliphatic and a colorless liquid. It has the formula C11H20O4 and the CAS registry number of 17557-23-2.[2] It has two oxirane groups per molecule.[3] Its principle use is in modifying epoxy resins.[4]

It is REACH registered.[5] The IUPAC name is 2-[[2,2-dimethyl-3-(oxiran-2-ylmethoxy)propoxy]methyl]oxirane.[6]

## Synthesis

[edit]

Neopentyl glycol and epichlorohydrin are reacted in the presence of a Lewis acid catalyst to form a halohydrin. This is followed by washing with sodium hydroxide in dehydrochlorination step. This forms Neopentyl glycol diglycidyl ether.[7] The waste products are water and sodium chloride and excess caustic soda. One of the quality control tests would involve measuring the Epoxy value by determination of the epoxy equivalent weight.

## Uses

[edit]

A key use is modifying the viscosity and properties of epoxy resins. As an Epoxy modifier it is classed as an epoxy reactive diluent.[8] which may then be formulated into CASE applications: Coatings,[9] Adhesives,[10] Sealants and Elastomers and composite materials. These uses include cationic polymerization reactions.[11][12] The use of the diluent does effect mechanical properties and microstructure of epoxy resins.[13][14] It is also used to synthesize other molecules.[15][16][17]

## Toxicity

[edit]

NPGDGE toxicity is fairly well understood.[18] It is classed as a skin irritant and skin sensitizer.[19][20]

## See also

[edit]

* Epoxide
* Glycidol

## References

[edit]

1. ^ "Neopentyl glycol diglycidyl ether". pubchem.ncbi.nlm.nih.gov. Retrieved 30 March 2022.
2. ^ "System of Registries | US EPA". sor.epa.gov. Retrieved 2022-03-25.
3. ^ PubChem. "Neopentyl glycol diglycidyl ether". pubchem.ncbi.nlm.nih.gov. Retrieved 2022-03-25.
4. ^ Jagtap, Ameya Rajendra; More, Aarti (2022-08-01). "Developments in reactive diluents: a review". Polymer Bulletin. 79 (8): 5667–5708\. doi:10.1007/s00289-021-03808-5. ISSN 1436-2449. S2CID 235678040.
5. ^ "Substance Information - ECHA". echa.europa.eu. Retrieved 2022-03-25.
6. ^ PubChem. "Neopentyl glycol diglycidyl ether". pubchem.ncbi.nlm.nih.gov. Retrieved 2022-03-29.
7. ^ Crivello, James V. (2006). "Design and synthesis of multifunctional glycidyl ethers that undergo frontal polymerization". Journal of Polymer Science Part A: Polymer Chemistry. 44 (21): 6435–6448\. Bibcode:2006JPoSA..44.6435C. doi:10.1002/pola.21761. ISSN 0887-624X.
8. ^ Monte, Salvatore J. (1998), Pritchard, Geoffrey (ed.), "Diluents and viscosity modifiers for epoxy resins", Plastics Additives: An A-Z reference, Polymer Science and Technology Series, vol. 1, Dordrecht: Springer Netherlands, pp. 211–216, doi:10.1007/978-94-011-5862-6_24, ISBN 978-94-011-5862-6, retrieved 2022-03-29
9. ^ Howarth G.A "Synthesis of a legislation compliant corrosion protection coating system based on urethane, oxazolidine and waterborne epoxy technology" page 23 Master of Science Thesis April 1997 Imperial College London
10. ^ Luo, Jing; Luo, Jianlin; Zhang, Jizhi; Bai, Yuanyuan; Gao, Qiang; Li, Jianzhang; Li, Li (September 2016). "A New Flexible Soy-Based Adhesive Enhanced with Neopentyl Glycol Diglycidyl Ether: Properties and Application". Polymers. 8 (9): 346. doi:10.3390/polym8090346. ISSN 2073-4360. PMC 6432166. PMID 30974622.
11. ^ Crivello, James V (March 2006). "Cationic photopolymerization of alkyl glycidyl ethers". Journal of Polymer Science Part A: Polymer Chemistry. 44 (9): 3036–3052\. Bibcode:2006JPoSA..44.3036C. doi:10.1002/pola.21419.
12. ^ Bulut, Umut; Crivello, James V. (2005-04-02). "Investigation of the Reactivity of Epoxide Monomers in Photoinitiated Cationic Polymerization". Macromolecules. 38 (9): 3584–3595\. Bibcode:2005MaMol..38.3584B. doi:10.1021/ma050106k. ISSN 0024-9297.
13. ^ Pastarnokienė, Liepa; Jonikaitė-Švėgždienė, Jūratė; Lapinskaitė, Neringa; Kulbokaitė, Rūta; Bočkuvienė, Alma; Kochanė, Tatjana; Makuška, Ričardas (2023-07-01). "The effect of reactive diluents on curing of epoxy resins and properties of the cured epoxy coatings". Journal of Coatings Technology and Research. 20 (4): 1207–1221\. doi:10.1007/s11998-022-00737-4. ISSN 1935-3804. S2CID 256749849.
14. ^ Khalina, Morteza; Beheshty, Mohammad Hosain; Salimi, Ali (2019-08-01). "The effect of reactive diluent on mechanical properties and microstructure of epoxy resins". Polymer Bulletin. 76 (8): 3905–3927\. doi:10.1007/s00289-018-2577-6. ISSN 1436-2449. S2CID 105389177.
15. ^ Simokaitiene, Jurate; Lazauskaite, Ruta; Grazulevicius, Juozas V (2002-02-28). "Photopolymerization of neopentyl glycol diglycidylether and its compositions with 9-(2-oxiranylmethyl) carbazole". Journal of Photochemistry and Photobiology A: Chemistry. 147 (1): 55–61\. doi:10.1016/S1010-6030(01)00622-0. ISSN 1010-6030.
16. ^ "Polyepoxy Compound Fixation / Yasuharu Noishiki, Teruo Miyata", Encyclopedia of Biomaterials and Biomedical Engineering (2 ed.), CRC Press, 2008, pp. 2263–2272, doi:10.1201/9780429154065-213, ISBN 978-0-429-15406-5, retrieved 2022-03-29
17. ^ Huang, Bi-wu; Huang, Bo-fen; Chen, Wei-qing; Ouyang, Zhi-qiang (2009-10-11). "Synthesis of a novel UV-curable prepolymer neopentyl glycol diglycidyl ether diacrylate and its cured film tensile property". Journal of Shanghai University (English Edition). 13 (5): 396. doi:10.1007/s11741-009-0511-3. ISSN 1863-236X. S2CID 124976924.
18. ^ Berdasco, Nancy Anne M.; Waechter, John M. (2012-08-17), Bingham, Eula; Cohrssen, Barbara; Powell, Charles H. (eds.), "Epoxy Compounds: Aromatic Diglycidyl Ethers, Polyglycidyl Ethers, Glycidyl Esters, and Miscellaneous Epoxy Compounds", Patty's Toxicology, Hoboken, NJ, USA: John Wiley & Sons, Inc., pp. 491–528, doi:10.1002/0471435139.tox083.pub2, ISBN 978-0-471-12547-1, retrieved 2022-07-28
19. ^ US EPA, OCSPP (2013-03-01). "Chemical Data Reporting under the Toxic Substances Control Act". www.epa.gov. Retrieved 2022-03-29.
20. ^ Jolanki, R.; Sysilampi, M.-L.; Kanerva, L.; Estlander, T. (1989). "Contact Allergy to Cycloaliphatic Epoxy Resins". In Frosch, Peter; Dooms-Goossens, A.; Lachapelle, J.-M.; Rycroft, R. J. G.; Scheper, R. J. (eds.). Current Topics in Contact Dermatitis. Berlin, Heidelberg: Springer. pp. 360–367\. doi:10.1007/978-3-642-74299-6_75. ISBN 978-3-642-74299-6.

## Further reading

[edit]

* Epoxy resin technology. Paul F. Bruins, Polytechnic Institute of Brooklyn. New York: Interscience Publishers. 1968. ISBN 0-470-11390-1. OCLC 182890.`{{cite book}}`: CS1 maint: others (link)
* Flick, Ernest W. (1993). Epoxy resins, curing agents, compounds, and modifiers : an industrial guide. Park Ridge, NJ. ISBN 978-0-8155-1708-5. OCLC 915134542.`{{cite book}}`: CS1 maint: location missing publisher (link)
* Lee, Henry (1967). Handbook of epoxy resins. Kris Neville ([2nd, expanded work] ed.). New York: McGraw-Hill. ISBN 0-07-036997-6. OCLC 311631322.
* "Dow Epoxy Resins" (PDF).

## External links

[edit]

* Hexion difunctional epoxy diluents
* Denacol epoxy diluent range
* Aalchem NPGDGE
* Cargill Reactive diluents

* v
* t
* e

Ethers of glycidol

Mono-epoxy|

* Allyl glycidyl ether
* n-Butyl glycidyl ether
* C12–C13 alcohol glycidyl ether
* C12–C14 alcohol glycidyl ether
* o-Cresyl glycidyl ether
* 2-Ethylhexyl glycidyl ether
* Phenyl glycidyl ether

Di-epoxy|

* Bisphenol A diglycidyl ether
* 1,4-Butanediol diglycidyl ether
* 1,4-Cyclohexanedimethanol diglycidyl ether
* Diethylene glycol diglycidyl ether
* Diglycidyl ether
* Diglycidyl resorcinol ether
* 1,6-Hexanediol diglycidyl ether
* Neopentyl glycol diglycidyl ether

Tri-epoxy|

* Castor oil glycidyl ether
* Trimethylolethane triglycidyl ether
* Trimethylolpropane triglycidyl ether

* Category

*[CID]: Compound ID
*[EPA]: U.S. Environmental Protection Agency
*[H315]: H315: Causes skin irritation
*[H317]: H317: May cause an allergic skin reaction
*[P261]: P261: Avoid breathing dust/fume/gas/mist/vapours/spray.
*[P264]: P264: Wash ... thoroughly after handling.
*[P272]: P272: Contaminated work clothing should not be allowed out of the workplace.
*[P280]: P280: Wear protective gloves/protective clothing/eye protection/face protection.
*[P302+P352]: P302+P352: IF ON SKIN: Wash with soap and water.
*[P321]: P321: Specific treatment (see ... on this label).
*[P332+P313]: P332+P313: If skin irritation occurs: Get medical advice/attention.
*[P333+P313]: P333+P313: If skin irritation or a rash occurs: Get medical advice/attention.
*[P362]: P362: Take off contaminated clothing.
*[P363]: P363: Wash contaminated clothing before reuse.
*[P501]: P501: Dispose of contents/container to ...
*[v]: View this template
*[t]: Discuss this template
*[e]: Edit this template